1. Field of Invention
The current invention relates to semiconductor compositions and devices that use the semiconductor compositions, and more particularly to pyromellitic diimide semiconductors and devices that include the pyromellitic diimide semiconductors.
2. Discussion of Related Art
The past decade has witnessed an increasing interest in organic thin film transistors (OTFTs) due to their applications in light-emitting displays, radio-frequency identification tags, and sensors, for example (Org. Electronics (Ed: H. Klauk), Wiley-VCH, Weinheim, Germany 2006; Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891; Anthony, J. E. Chem. Rev. 2006, 106, 5028; Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359; Yang, R. D.; Gredig, T.; Colesniuc, C. N.; Park, J.; Schuller, I. K.; Trogler, W. C.; Kummel, A. C. Appl. Phys. Lett. 2007, 90, 263506; Huang, J.; Miragliotta, J.; Becknell, A.; Katz, H. E. J. Am. Chem. Soc. 2007, 129, 9366). Organic semiconductors can function either as a p-channel or n-channel charge carrier. While many organic materials can be used for p-channel OTFTs, there is only a limited number of available organic materials that can be used for n-channel OTFTs (Org. Electronics (Ed: H. Klauk), Wiley-VCH, Weinheim, Germany 2006; Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891; Anthony, J. E. Chem. Rev. 2006, 106, 5028; Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359; Yang, R. D.; Gredig, T.; Colesniuc, C. N.; Park, J.; Schuller, I. K.; Trogler, W. C.; Kummel, A. C. Appl. Phys. Lett. 2007, 90, 263506; Mori, T. J. Phys.: Condens. Matter 2008, 20, 184010; Gao, X; Wang, Y; Yang, X; Liu, Y; Qiu, W; Wu, W; Zhang, H; Qi, T.; Liu, Y.; Lu, K; Du, C.; Shuai Z.; Yu, G. and Zhu, D. B. Adv. Mater. 2007, 19, 3037). Therefore, there is a need for more n-channel materials with high mobility and stability, for example to allow for combining n-channel and p-channel transistors in complementary circuits which have advantages of low power dissipation, low noise and greater operational stability (Crone, B.; Dodabalapur, A.; Lin, Y. Y.; Filas, R. W.; Bao, Z.; LaDuca, A.; Sarpeshkar, R.; Katz, H. E.; Li, W. Nature 2000, 403, 521; Hizu, K.; Sekitani, T.; Someya, T.; Otsuki, J. Appl. Phys. Lett. 2007, 90, 093504). Since the report of naphthalenetetracarboxylic diimides as air stable n-channel materials with mobility up to 0.1 cm2/(V.s), a large number of n-channel materials have been based on either naphthalene or perylene tetracarboxylic diimides (Laquindanum, J. G.; Katz, H. E.; Dodabalapur, A.; Lovinger, A. J. J. Am. Chem. Soc. 1996, 118, 11331; Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y. Y.; Dodabalapur, A. Nature 2000, 404, 478; Jones, B. A.; Ahrens, M. J.; Yoon, M.-H.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Angew. Chem. Int. Ed. 2004, 43, 6363; Jones, B. A.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Chem. Mater. 2007, 19, 2703; Jones, B. A.; Facchetti, A.; Wasielewski, M. R.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 15259; Chen, H. Z.; Ling, M. M.; Mo, X.; Shi, M. M.; Wang, M.; Bao, Z. Chem. Mater. 2007, 19, 816; Schmidt, R.; Ling, M. M.; Oh, J. H.; Winkler, M.; Konemann, M.; Bao, Z.; Wurthner, F. Adv. Mater. 2007, 19, 3692; Weitz, R. T.; Amsharov, K.; Zschieschang, U.; Villas, E. B.; Goswami, D. K.; Burghard, M.; Dosch, H.; Jansen, M.; Kern, K.; Klauk, H. J. Am. Chem. Soc. 2008, 130, 4637; See, K. C.; Landis, C.; Sarjeant, A.; Katz, H. E. Chem. Mater. 2008, 20, 3609; Oh, J. H.; Liu, S.; Bao, Z.; Schmidt, R.; Wurthner, F. Appl. Phys. Lett. 2007, 91, 212107-3). Recently, several anthracene tetracarboxylic diimides were synthesized by Marks et al through multi-step reactions and found to be good n-channel materials with high on-off ratios (Wang, Z.; Kim, C.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 13362). The common structural features, the tetracarboxylic diimides, were flanked on both sides of the planar aromatic rings, which were varied from two-ring naphthalene to three-ring anthracene, and finally to five-ring perylene.
Though pyromellitic dimides are best known as segments of highly insulating polyimide dielectrics, it is nevertheless appears that no attempt has been made to fabricate transistors from pyromellitic diimide derivatives, which have the simplest aromatic ring (benzene) in the center, and the tetracarboxylic diimides on both sides of the benzene ring. Pyromellitic diimide derivatives can be easily prepared by one-step reaction between pyromellitic dianhydride and various amines. Thus, there remains a need for improved organic semiconductors and devices that use the improved organic semiconductors